<i>N</i>-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycine–Water (1/2)

Low, John N.; Ferguson, George; López, Rafael; Arranz‐Mascarós, Paloma; Cobo, Justo; Bazzicalupi, Carla; Nogueras, Manuel; Sánchez, Alfredo Hernández

doi:10.1107/s0108270197003934

Cited by 8 publications

(13 citation statements)

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“…For isolated molecules of (1)±(5) two conformational minima were found in the rotation of the substituent around the bond N2ÐC21. For (1) the two conformers were mirror images, with identical ÁH f 0 values at the minima and calculated torsional angles C2ÐN2ÐC21Ð C211 of AE79.3 , remarkably close to the observed values of À81.3 (3) (Low et al, 1997). For each of (2)±(5) again two conformational minima were found, but with marginally different torsional angles and ÁH f 0 values, because of the stereogenic centre at C21 which precludes the conformers from being mirror images.…”

Section: Modelling the Molecular And Electronic Structuressupporting

confidence: 65%

“…For (1) see Low et al (1997) and for (2) see Low et al (1999) [original atom-labelling altered to be consistent with that in (3)±(5)].…”

Section: Resultsmentioning

confidence: 99%

“…The crystal structures of (1) (Low et al, 1997) and (2) (Low et al, 1999) are both characterized by very short intermolecular OÐHÁ Á ÁO hydrogen bonds involving the carboxylic acid function as the hydrogen-bond donor and the nitrosyl O atom .…”

Section: Introductionmentioning

confidence: 99%

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N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) derivatives of glycine, valine, serine, threonine and methionine: interplay of molecular, molecular–electronic and supramolecular structures

Low

López

Arranz‐Mascarós

et al. 2000

Acta Crystallogr Sect B

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In each of N-(6-amino-3, 4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)valine, C(10)H(15)N(5)O(4) (3) (orthorhombic, P2(1)2(1)2(1)), N-(6-amino-3, 4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)serine monohydrate, C(8)H(11)N(5)O(5).H(2)O (4) (orthorhombic, P2(1)2(1)2(1)), and N-(6-amino-3, 4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)threonine, C(9)H(13)N(5)O(5)(5) (monoclinic, P2(1)), the C-nitroso fragments exhibit almost equal C-N and N-O bond lengths: the C-N range is 1. 315 (3)-1.329 (3) A and the N-O range is 1.293 (3)-1.326 (3) A. In each compound there are also very short intermolecular O-H.O hydrogen bonds, in which carboxyl groups act as hydrogen-bond donors to the nitrosyl O atoms: the O.O distances range from 2.440 (2) to 2. 504 (4) A and the O-H.O angles lie between 161 and 163 degrees. An interpretation of the relationship between the unusual intramolecular bond lengths and the very short intermolecular hydrogen bonds has been developed based on database analysis and computational modelling. In each of (3)-(5) there is an extensive network of intermolecular hydrogen bonds, generating three-dimensional frameworks in (3) and (5), and two-dimensional sheets in (4).

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Section: Modelling the Molecular And Electronic Structuressupporting

confidence: 65%

“…For (1) see Low et al (1997) and for (2) see Low et al (1999) [original atom-labelling altered to be consistent with that in (3)±(5)].…”

Section: Resultsmentioning

confidence: 99%

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N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) derivatives of glycine, valine, serine, threonine and methionine: interplay of molecular, molecular–electronic and supramolecular structures

Low

López

Arranz‐Mascarós

et al. 2000

Acta Crystallogr Sect B

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“…All the resulting products, 3b-f, were fully characterized through elemental analysis, spectroscopic properties (ir, uv-vis, ms, 1 H-nmr and 13 C-nmr, see Experimental and Table 2) and single crystal X-ray diffraction analysis of one of them (3e) [9]. A remarkable structural feature of compounds 3a-g (also observed in their precursors, 1a-c) is the strong intramolecular hydrogen bond established between the 5-nitroso and the 6-NH groups, which causes the pmr signal of the involved NH proton to be displaced up to 10.84-10.94 ppm for 3a-f and even further (up to 98…”

Section: Jan-feb 2002 97mentioning

confidence: 99%

Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Marchal

Nogueras

Sánchez

et al. 2002

Journal of Heterocyclic Chem

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The nucleophilic substitution of 2‐mefhoxy groups in pyrimidine derivatives was strongly activated by introduction of a 5‐nitroso group on to the pyrimidine ring. The aminolysis of several 2‐methoxy‐5‐nitrosopyrimidine derivatives was performed at room temperature in hydroxylic as well as in non‐hydroxylic media with different primary amines in short time and good yields. The aminolysed substrates include 6‐[(per‐O‐acetyl)glycosyl]aminopyrimidines which afforded the corresponding 2‐aminopyrimidines without harming the acetyl protecting groups of the sugar moiety.

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“…The neutral compound LH was prepared according to the reported method (Low et al, 1997) and the corresponding ammonium salt [NH 4 ] + L À was obtained by addition of ammonia to an aqueous solution of LH. Compounds (1)±(3) were prepared by the addition of the corresponding amount of the metal chloride (LiCl, NaCl or KCl) to a stirred aqueous solution of [NH 4 ] + L À .…”

Section: Synthesismentioning

confidence: 99%

Hydrated metal complexes of N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycinate: interplay of molecular, molecular–electronic and supramolecular structures

Low¹,

Sánchez²,

Arranz‐Mascarós³

et al. 2001

Acta Crystallogr Sect B

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The title anion, (C(7)H(8)N(5)O(4))(-), L(-), forms hydrated metal complexes with a range of metal ions M(+) and M(2+). Lithium and manganese(II) form finite molecular aggregates [Li(L)(H(2)O)(3)] (1) and [Mn(L)(2)(H(2)O)(4)].6H(2)O (4) in which the molecular aggregates are linked into three-dimensional frameworks by extensive hydrogen bonding. The sodium and potassium derivatives, [Na(2)(L)(2)(H(2)O)(3)] (2) and [K(L)(H(2)O)] (3) both form organic-inorganic hybrid sheets in which metal-oxygen ribbons are linked by strips containing only organic ligands: these sheets are linked by hydrogen bonds into three-dimensional frameworks. In (2) the metal-oxygen ribbon is built from pairs of edge-shared trigonal bipyramids linked by water molecules, while in (3) it consists of a continuous chain of vertex-sharing octahedra. The nitroso group in the anion acts as an eta(1) ligand towards Na(+) and as an eta(2) ligand towards K(+). In all cases the anion L(-) shows the same unusual pattern of interatomic distances as the neutral parent LH.

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N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycine–Water (1/2)

Cited by 8 publications

References 0 publications

N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) derivatives of glycine, valine, serine, threonine and methionine: interplay of molecular, molecular–electronic and supramolecular structures

N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) derivatives of glycine, valine, serine, threonine and methionine: interplay of molecular, molecular–electronic and supramolecular structures

Aminolysis of methoxy groups in pyrimidine derivatives. Activation by 5‐nitroso

Hydrated metal complexes of N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycinate: interplay of molecular, molecular–electronic and supramolecular structures

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